The Remarkable Fools Letter

The Remarkable Fools Letter

once upon a time five years ago

the last few months asked: “you fool, is this the end?”

Jim Dalling's avatar
Jim Dalling
Jan 17, 2026
∙ Paid

Aloha dear reader,

We’re approaching the 5 year anniversary of the Foolsletter here.

When I was working, helping Ricky in the delivery truck, I was concerned that I couldn’t make it this far.

My back was sore, my throat exhausted and every cell of my being buzzed from the vibration of the thunder truck.

Every day I felt lost.

Every day writing was a chore.

Every day before I wrote, I thought to myself Jimmy, what the hell do you have to say anyway?

And every day I’d tell myself to just do the work and keep going.

And now that I’m no longer an employee of a global logistics company, big things are in motion.

Last year, I did a lot of ultra distance bike riding and fell in love with tour guiding.

This year?

This year is the second lap of both.

And now during the heart of winter?

I’m preparing for both.

And so far things are a lot more clear this second time around.

But that’s how things go on a bike.

You need to hit a trail three times, the first time you experience it, the second time you have an ide…

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